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Vinyl Cation Stabilization by Silicon Enables a Formal Metal-Free ?-Arylation of Alkyl Ketones.

ABSTRACT: The ability of silicon to stabilize vinyl cationic species leads to a redox arylation of alkynes whereby the stringent limitations of reactivity and regioselectivity of alkyl-substituted alkynes are lifted. This allows the synthesis of a range of ?-silyl-?'-arylketones under mild conditions in good to excellent yields and with high functional group tolerance, whereby the silicon moiety in the final products can either be removed for a formal acetone monoarylation transform, or capitalized upon for subsequent electrophilic substitutions at either side of the carbonyl group.

SUBMITTER: Pons A

PROVIDER: S-EPMC6899746 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Vinyl Cation Stabilization by Silicon Enables a Formal Metal-Free α-Arylation of Alkyl Ketones.

Pons Amandine A Michalland Jean J Zawodny Wojciech W Chen Yong Y Tona Veronica V Maulide Nuno N

Angewandte Chemie (International ed. in English) 20191022 48

The ability of silicon to stabilize vinyl cationic species leads to a redox arylation of alkynes whereby the stringent limitations of reactivity and regioselectivity of alkyl-substituted alkynes are lifted. This allows the synthesis of a range of α-silyl-α'-arylketones under mild conditions in good to excellent yields and with high functional group tolerance, whereby the silicon moiety in the final products can either be removed for a formal acetone monoarylation transform, or capitalized upon f ...[more]

PMID: 31638738

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